ChemFOnt: Showing chemical card for Cer(d18:1/23:0) (CFc000000758)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:45:15 UTC

Chemfont ID

CFc000000758

Molecule Identification

Common Name

Cer(d18:1/23:0)

Definition

Ceramides, also known as N-acylsphingosines, consist of a sphingoid base linked to a fatty acid chain via the amine group. Ceramides are one of the hydrolysis byproducts of sphingomyelin via the enzyme sphingomyelinase (sphingomyelin phosphorylcholine phosphohydrolase, E.C.3.1.4.12) which has been identified in the subcellular fractions of human epidermis and many other tissues (PMID: 25935 ). They can also be synthesized from serine and palmitate in a de novo pathway and are regarded as important cellular signals for inducing apoptosis (PMID: 14998372 ). Ceramides are key to the biosynthesis of glycosphingolipids and gangliosides. Cer(d18:1/23:0), in particular, consists of a monounsaturated 18-carbon dihydroxylated sphingoid base linked to one chain of tricosanoic acid. Cer(d18:1/23:0) has been identified in the stratum corneum by reversed-phase HPLC coupled with APPI–MS (PMID: 17027012 ). It has been found in human blood plasma by gas-liquid chromatography on high temperature polarizable capillary columns (PMID: 2755317 , 8354950 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
N-(Tricosanoyl)-sphing-4-enine	ChEBI
N-[(1S,2R,3E)-2-Hydroxy-1-(hydroxymethyl)-3-heptadecen-1-yl]-tricosanamide	HMDB
N-[(1S,2R,3E)-2-Hydroxy-1-(hydroxymethyl)-3-heptadecenyl]-tricosanamide	HMDB
[R-[R,s-(e)]]-N-[2-hydroxy-1-(hydroxymethyl)-3-heptadecenyl]-tricosanamide	HMDB
Ceramide	HMDB
Ceramide(D18:1/23:0)	HMDB
N-(Tricosanoyl)-sphingosine	HMDB
N-(Tricosanoyl)-D-erythro-sphingosine	HMDB
N-(Tricosanoyl)-4-sphingenine	HMDB
N-(Tricosanoyl)-D-sphingosine	HMDB
N-(Tricosanoyl)-sphingenine	HMDB
N-(Tricosanoyl)-erythro-4-sphingenine	HMDB
C23-Ceramide	HMDB
Ceramide (D18:1,C23:0)	HMDB
Cer(d18:1/23:0)	HMDB

Chemical Formula

C₄₁H₈₁NO₃

Average Molecular Weight

636.0867

Monoisotopic Molecular Weight

635.621645463

IUPAC Name

N-[(2S,3R,4E)-1,3-dihydroxyoctadec-4-en-2-yl]tricosanamide

Traditional Name

N-[(2S,3R,4E)-1,3-dihydroxyoctadec-4-en-2-yl]tricosanamide

CAS Registry Number

67605-84-9

SMILES

[H][C@@](CO)(NC(=O)CCCCCCCCCCCCCCCCCCCCCC)[C@H](O)\C=C\CCCCCCCCCCCCC

InChI Identifier

InChI=1S/C41H81NO3/c1-3-5-7-9-11-13-15-17-18-19-20-21-22-23-25-27-29-31-33-35-37-41(45)42-39(38-43)40(44)36-34-32-30-28-26-24-16-14-12-10-8-6-4-2/h34,36,39-40,43-44H,3-33,35,37-38H2,1-2H3,(H,42,45)/b36-34+/t39-,40+/m0/s1

InChI Key

NAJHAHQNQCNWOP-PUYNVXOJSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as ceramides. These are lipid molecules containing a sphingosine in which the amine group is linked to a fatty acid.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Sphingolipids

Sub Class

Ceramides

Direct Parent

Ceramides

Alternative Parents

Substituents

Ceramide
Fatty amide
N-acyl-amine
Fatty acyl
Carboxamide group
Secondary alcohol
Secondary carboxylic acid amide
Carboxylic acid derivative
Primary alcohol
Organooxygen compound
Organonitrogen compound
Organic oxide
Organopnictogen compound
Organic oxygen compound
Alcohol
Organic nitrogen compound
Carbonyl group
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

N-acylsphingosine (CHEBI:84372 )
N-acylsphingosines (ceramides) (LMSP02010021 )

Functional Ontology

Physiological effect

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 20671299)

Cellular substructure

Membrane (HMDB: HMDB0000950)
Endosome (HMDB: HMDB0000950)
Extracellular (HMDB: HMDB0000950)
Golgi apparatus membrane (PMID: 12408751)
Cell membrane (PMID: 12408751)
Cell membrane (HMDB: HMDB0000950)
Intracellular membrane (HMDB: HMDB0000950)

Organelle

Endoplasmic reticulum (PMID: 12408751)

Cell

All cells and tissues (HMDB: HMDB0000950)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0000950)

Source

Endogenous

Endogenous (HMDB: HMDB0000950)

Animal

Animal (HMDB: HMDB0000950)

Exogenous

Food

Food (HMDB: HMDB0000950)

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Exogenous (HMDB: HMDB0000950)

Process

Naturally occurring process

Biological process

Cellular process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0000950)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0000950)

Insulin signaling pathway (HMDB: HMDB0000950)

Biochemical process

Lipid transport (HMDB: HMDB0000950)

Role

Biological role

Molecular messenger

Signaling molecule (HMDB: HMDB0000950)

Modulator

Insulin signaling antagonist (HMDB: HMDB0000950)

Industrial application

Food and nutrition

Food additive (HMDB: HMDB0000950)

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0000950)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	2.4e-05 g/L	ALOGPS
logP	10.29	ALOGPS
logP	13.98	ChemAxon
logS	-7.4	ALOGPS
pKa (Strongest Acidic)	13.62	ChemAxon
pKa (Strongest Basic)	-1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	69.56 Å²	ChemAxon
Rotatable Bond Count	37	ChemAxon
Refractivity	197.98 m³·mol⁻¹	ChemAxon
Polarizability	87.82 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0000950

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022334

KNApSAcK ID

Not Available

Chemspider ID

24765757

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

5896

PubChem Compound

52931115

PDB ID

Not Available

ChEBI ID

84372

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Gaudin, K.; Lesellier, E.; Chaminade, P.; Ferrier, D.; Baillet, A.; Tchapla, A. Retention behaviour of ceramides in sub-critical fluid chromatography in comparison with non-aqueous reversed-phase liquid chromatography. Journal of Chromatography, A (2000), 883(1+2), 211-222

Showing chemical card for Cer(d18:1/23:0) (CFc000000758)

MOL for CFc000000758 (Cer(d18:1/23:0))

3D MOL for CFc000000758 (Cer(d18:1/23:0))

3D SDF for CFc000000758 (Cer(d18:1/23:0))

3D-SDF for CFc000000758 (Cer(d18:1/23:0))

PDB for CFc000000758 (Cer(d18:1/23:0))

3D PDB for CFc000000758 (Cer(d18:1/23:0))

SMILES for CFc000000758 (Cer(d18:1/23:0))

INCHI for CFc000000758 (Cer(d18:1/23:0))

Structure for CFc000000758 (Cer(d18:1/23:0))

3D Structure for CFc000000758 (Cer(d18:1/23:0))